Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Healdsburg vacation rentals

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (139 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is CA $127
CA $145 total
includes taxes & fees
Dec 6 - Dec 7
Wildhaven Sonoma Glamping
A residential property with a curved driveway, stone walls, and palm trees.

2. Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg

Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg
Healdsburg
The price is CA $328
CA $560 total
includes taxes & fees
Nov 11 - Nov 12
Hilltop Overlook Room with Views | Private Entrance | Near Downtown Healdsburg
A hot tub on a wooden deck with a view of a forested area.

3. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.4 out of 10, Exceptional, (10 reviews)
"Very unique and charming property. Definitely felt like being in a tree house in the redwoods. We spent most of our time when there sitting on the deck. It was conveniently located to everything we wanted to do - drive to the coast, hike at the state park, and visit nearby restaurants and wineries."
United States
Sherri
The price is CA $403
CA $860 total
includes taxes & fees
Nov 21 - Nov 22
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

4. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"Wonderful vacation and location. "
United States
Leslie M.
The price is CA $568
CA $1,447 total
includes taxes & fees
Nov 9 - Nov 10
River View Lodge - Hot Tub and Tastings Included
A modern building with a metal exterior, a wooden door, and a small window on the side.

5. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is CA $228
CA $528 total
includes taxes & fees
Dec 3 - Dec 4
Country Carriage House in Downtown Geyserville, Vineyard Views
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

6. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is CA $239
CA $539 total
includes taxes & fees
Dec 2 - Dec 3
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A wooden interior with a dining area, a bench, and a mirror on the wall.

7. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (30 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is CA $178
CA $643 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Riverfront Cabin - Beach Access & Wood Stove
Private kitchen

8. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is CA $152
CA $486 total
includes taxes & fees
Nov 9 - Nov 10
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A patio with a grill, outdoor seating, and a house with a covered porch.

9. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is CA $406
CA $1,442 total
includes taxes & fees
Nov 29 - Nov 30
Sauna, Cold Plunge & Fire Pit Near Wineries
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

10. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is CA $231
CA $495 total
includes taxes & fees
Nov 9 - Nov 10
Wine Country Cottage Escape
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

11. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is CA $312
CA $786 total
includes taxes & fees
Nov 8 - Nov 9
Russian River Retreat: Private Beach & DogFriendly
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

12. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (70 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A cozy room with a large window, a blue sofa, a wooden cabinet, and a patterned rug.

13. Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
Forestville
The price is CA $432
CA $898 total
includes taxes & fees
Dec 2 - Dec 3
Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

14. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (40 reviews)
"Stayed here on a couples trip to Napa and Sonoma. It was a perfect home base for the trip, had everything we needed and the two masters suites were almost identical which was a nice bonus so both couples felt equally comfortable."
United States
Chris N.
Vineyard Vue - Wine Tastings Included
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

15. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (10 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
The price is CA $256
CA $704 total
includes taxes & fees
Nov 11 - Nov 12
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A wooden cabin with a porch, surrounded by tall trees.

16. Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.4 out of 10, Very good, (15 reviews)
"Great place to stay clean quiet peaceful loved it "
United States
Josie B.
The price is CA $175
CA $421 total
includes taxes & fees
Nov 12 - Nov 13
Enchanting Retreat in the heart of Redwoods
A modern interior with a kitchen, dining area, and living room.

17. Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (13 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is CA $211
CA $464 total
includes taxes & fees
Nov 9 - Nov 10
Tranquil Redwood Retreat
A patio with outdoor seating, a hot tub, and string lights.

18. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (50 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is CA $905
CA $1,764 total
includes taxes & fees
Nov 9 - Nov 10
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A wooden house with a stone staircase leading to a deck, surrounded by palm trees and a stone wall.

19. Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar

Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
Geyserville
9.2 out of 10, Wonderful, (23 reviews)
"Spacious and beautiful property- we had a great time!"
United States
Kirsten G.
The price is CA $874
CA $1,547 total
includes taxes & fees
Nov 9 - Nov 10
Alexander Valley Lodge w/ Pool, Hot tub, Waterfall, Pool table and Tiki Bar
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

20. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is CA $496
CA $1,376 total
includes taxes & fees
Nov 9 - Nov 10
Elegant Vineyard Living at a Private Wine Country Estate
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Healdsburg Hotel Reviews

A stone fireplace with a fire, outdoor seating with chairs and a table, and a sign reading "Rancho Cayman Inn".
Rancho Caymus Inn

Rancho Caymus Inn

Rancho Caymus Inn
St. Helena

10/10 Excellent

Perfect little retreat.
Canada
Grant
Reviewed October 30, 2026
Rancho Caymus Inn

Find out more about Healdsburg

Everything you need to know about Healdsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Healdsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Healdsburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Healdsburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Healdsburg. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Healdsburg vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Healdsburg vacation rentals we have selected for you start as low as CA $127 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Healdsburg rentals

At Expedia, we put the best Healdsburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Healdsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Healdsburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Healdsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near Healdsburg Center for the Arts, or you can choose a secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What's the top vacation rental that Healdsburg has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This vacation home rental outside of Healdsburg is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Healdsburg?

Expedia has 135 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Russian River and Healdsburg Ridge Open Space Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include SingleThread Farm at Dry Creek. Healdsburg Plaza and Jordan Vineyard & Winery are other places to visit while you're in town.

What are vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.